benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate | 1616628-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate
• CAS: 1616628-06-8
• 化学式: C₅₁H₅₀Cl₃NO₁₅
• 分子量: 1023.31
• InChiKey: HSGCWMUHVIAWDF-MDKCBPMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  70.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  192.84
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  O-(benzyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate) trichloroacetimidate 、 benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以41%的产率得到4-methoxyphenyl O-(benzyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronate
  参考文献：
  名称：

  Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

  摘要：

  The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.007
• 作为产物：
  描述：

  2,2,2-trichloro-N-((2R,4aR,6S,7R,8R,8aS)-6-(((2,3-dimethylbutan-2-yl)dimethylsilyl)oxy)-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 pyridine hydrofluoride 、 三氟甲磺酸三甲基硅酯 、 一水合肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 128.16h， 生成 benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate
  参考文献：
  名称：

  Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

  摘要：

  The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.007